4-Nitrobenzoic Acid → HCID 118101240, compound

Participants

Reaction Steps

Intermediate 27C (250 mg, 0.595 mmol) was mixed with 4-nitrobenzoic acid (447 mg, 2.68 mmol), PPh3 (741 mg, 2.82 mmol) in THF (1.5 mL) and stirred at rt for 10 min. The reaction was cooled to 0° C., then DIAD (0.589 mL, 2.97 mmol) was added. After stirring at rt for 16 h, the reaction was quenched with H2O and extracted with EtOAc (2×). The organic extracts were washed with brine, dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography to give 27D (268 mg, 0.471 mmol, 79% yield) as a white foam. The relative stereochemistry of hydroxyether is cis however absolute stereochemistry is undetermined MS (ESI) m/z: 570.4 (M+H)+.

Provenance & Evidence